Chemistry:Piperidylthiambutene
From HandWiki
Short description: Chemical compound
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| Formula | C17H21NS2 |
| Molar mass | 303.48 g·mol−1 |
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| Melting point | 188 to 189 °C (370 to 372 °F) |
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Piperidylthiambutene (Piperidinohton) is a synthetic[1] opioid analgesic drug from the thiambutene family, which has around the same potency as morphine.[2][3][4] Piperidylthiambutene is structurally distinct from fentanyl, its analogues, and other synthetic opioids previously reported.[1] If sold or obtained for the purpose of human consumption it could be considered a controlled substance analogue in some countries such as the US, Australia and New Zealand. Piperidylthiambutene has been sold as a designer drug, first appearing in late 2018.[5][6]
Synthesis
Patent:[7]
The Grignard reaction between 3-Piperidinobutyric acid ethyl ester, CID:10774378 (1) and 2-Bromothiophene [1003-09-4] (2) gives 3. Dehydration in acid completes the synthesis.
References
- ↑ 1.0 1.1 "Piperidylthiambutene". https://www.npsdiscovery.org/wp-content/uploads/2019/09/Piperidylthiambutene_091819_NMSLabs_Report.pdf.
- ↑ "A new series of analgesics". Nature 165 (4186): 122. January 1950. doi:10.1038/165122a0. PMID 15409854. Bibcode: 1950Natur.165..122A.
- ↑ "Dithienylbutylamines as analgesics". Nature 167 (4239): 153–4. January 1951. doi:10.1038/167153b0. PMID 14806409. Bibcode: 1951Natur.167..153A.
- ↑ "Analgesic and other properties of 3: 3-dithienylalkenylamines". British Journal of Pharmacology and Chemotherapy 8 (1): 2–9. March 1953. doi:10.1111/j.1476-5381.1953.tb00739.x. PMID 13066683.
- ↑ "Analytical report Piperidylthiambutene.". European Project Response. November 2018. https://www.policija.si/apps/nfl_response_web/0_Analytical_Reports_final/Piperidylthiambutene-ID-2034-18_report.pdf.
- ↑ "In vitro functional characterization of a panel of non-fentanyl opioid new psychoactive substances". Archives of Toxicology 94 (11): 3819–3830. November 2020. doi:10.1007/s00204-020-02855-7. PMID 32734307. https://biblio.ugent.be/publication/8687070.
- ↑ Adamson Donald Wallace, U.S. Patent 2,561,899 (1951 to Burroughs Wellcome Co).
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